Jonny was a part of Reading's youth academy but didn't make a senior appearances for them as he went out on loan to Forest Green Rovers and the MK Dons for the ends of the 2005/06 and 2006/07 seasons respectively. He left the club at the end of the 2006/07 season and joined Leicester City in June 2007.

He made seven league appearances for Leicester in the 2007/08 season before going out on loan to Northampton Town. The following season saw him go out on loan once more, this time to Cheltenham Town. He left Leicester City at the end of the 2009/10 season by mutual consent and joined Inverness Caledonian Thistle in July 2009.

He had a successful three seasons at Inverness, winning the First Division in the first and racking up just over one hundred appearances for the club in all competitions. In June 2012, Jonny moved to SPL rivals Aberdeen. He has since made over one hundred league appearances for the club and won the Scottish League Cup in 2013/14 season. In June 2017 it was announced that Jonny had signed with Scottish Champions Celtic.

Jonny has been capped for the Republic of Ireland and, ahead of the friendlies with the Netherlands and Belarus, with 2 caps to his name. He was not included in the Republic of Ireland's final squad for the 2016 European Championship.

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